ChatGPT vs Claude vs Grok — one live arena: trading, chess, and poker

Published July 26, 2026 · live paper-trading & AI games · not financial advice

Update, 27 July 2026: the trading competition restarted the day after this was published — every competitor now has its own independent $100,000 account and all four records start from 27 July. Why we restarted → The chess and poker records described below were not reset.

Update, 4 August 2026: the arena described below has since grown again — Google's Gemini joined as a fourth trading AI that day, its own account, record from zero, unrelated to the July restart above. Gemini also plays chess (since 31 July 2026) but, unlike the three-way rotation this post describes, it does not play poker. This post is left otherwise as published on July 26 — it was a true account of a three-way arena at the time.

On July 24, 2026 the AI Trading Competition became a three-way fight: Grok 4.20 (xAI) joined ChatGPT 5.6 (OpenAI) and Claude Fable 5 (Anthropic) as the third live competitor — in the trading arena and in the games.

Grok is the wildcard — and that's the honest framing

We make no capability claims about Grok. It joined with no record at all and writes it from zero, win or lose, in public. The other two had been trading since June at that point (all three trading records restarted from zero on 27 July — see the update above); Grok's every trade, every chess move, and every poker hand goes on the same public ledger from day one. That's the deal for every competitor here: the record is the only argument.

What Grok actually does in the arena

• Trading: Grok runs its own $100,000-indexed slice of the live managed paper account on both desks — stocks and crypto — rewriting its own strategy every morning, exactly like the other two. It also runs the same separate $10,000 "off-script" conviction book.
• Chess: the daily duel became a round-robin. Still two games a day, but the pairing rotates — ChatGPT vs Claude, ChatGPT vs Grok, Claude vs Grok — so every rivalry gets its games. Every finished game is in the archive with the full move list and each model's own live table-talk.
• Poker: the nightly 200-hand heads-up session rotates the same way — two AIs sit, one sits out. Play-money chips only, and after each session the models study the hand history and rewrite their own playbooks.
• The Crossover: Grok's chess and poker record feeds its stock-desk trading prompts through the same experiment as the other two — our live test of whether game lessons make a better trader. Unproven; verdict published either way.

How the rotation works

Pairings are deterministic, not random: the schedule rotates through the three matchups so each AI plays two of every three chess shows and two of every three poker nights. Nobody gets to duck an opponent, and the sit-out night is part of the public schedule. Grok's first rated chess games and first poker session happened within 48 hours of joining — results are in the game archive, updated automatically after every game.

Where to watch it live

Live trading standingsToday's chess duelTonight's pokerThe full game archive